


P.Y.T.

by Thatmalu



Category: IT (1990), IT (Movies - Muschietti), IT - Stephen King
Genre: Aftercare, Anal Fingering, Anal Sex, Ass Play, Big dick humiliation, Bisexual Richie Tozier, Bottom Eddie Kaspbrak, College Students Eddie Kaspbrak/Richie Tozier, Crying, Daddy Kink, Dresses, Eddie Kaspbrak Has a Big Dick, Eddie Kaspbrak Loves Richie Tozier, Eddie Kaspbrak/Richie Tozier-centric, Established Eddie Kaspbrak/Richie Tozier, Face Slapping, Face-Fucking, Feminization, Gay Eddie Kaspbrak, Humiliation, Light CBT, Light Dom/sub, Light Sadism, M/M, Misgendering, Richie Tozier Loves Eddie Kaspbrak, Rough Oral Sex, Soft Eddie Kaspbrak, Soft Richie Tozier, Top Richie Tozier, You heard me, gagging, lots of lube
Language: English
Status: Completed
Published: 2021-02-14
Updated: 2021-02-14
Packaged: 2021-03-14 10:46:58
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,501
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29417358
Author URL: https://archiveofourown.org/users/Thatmalu/pseuds/Thatmalu
Summary: Eddie thinks he’s the only person who could possibly be disappointed in having a big dick.Yeah, you read that right. It’s the Big Dick Humiliation fic no one needed but I wrote anyway.
Relationships: Eddie Kaspbrak/Richie Tozier
Comments: 19
Kudos: 131





	P.Y.T.

**Author's Note:**

  * For [ghostnebula](https://archiveofourown.org/users/ghostnebula/gifts).



> Happy Valentine’s Day Sierra you beautiful bastard! Inspiration and loml 💕 
> 
> I want you all the imagine Richie singing P.Y.T. to Eddie and make your day ❤️

Eddie thinks he’s the only person who could possibly be disappointed in having a big dick.

It’s not that he doesn’t enjoy having one in general, and he can definitely attest to that the first time Richie goes down on him. He just about loses his mind feeling Richie’s drool drip down his shaft and looking down to see those startling blue eyes staring back up at him while he has a vice grip in Richie’s hair. Richie seems to like it and was actively surprised after seeing it for the first time.

“How does this not slip out the hems of your little booty shorts?”

“Shut the fuck up, asshole,” Eddie had laughed in embarrassment.

But Eddie kind of likes that embarrassment and he thinks that’s where some of the problems stem from. He likes feeling small in Richie’s arms and being called cute and little and he melts now when Richie calls him _pretty._ It’s not so much with other people who make him feel small out of malice, but when Richie towers over him in the bed and looks like he could swallow Eddie whole. So there’s a part of him that wonders if that’s why he wishes his dick _matched_ the rest of him like a normal person. It’s not as big as Richie’s and realistically it’s not a laughable comparison; it’s not like it looks _comically_ huge. He knows it’s weird but it gives Eddie this dull sensation in his gut to think about.

One day, Richie is over in Eddie’s dorm and he’s got Eddie’s legs spread out around his waist. It’s midday and they're trying not to make too much noise that might echo down the hall, but the mattress is squeaking and Eddie can’t shut the fuck up when there’s a dick in his ass if his life depended on it. Hell, _neither_ of them can be quiet when fucking, and Richie is trying not to laugh at the sound of the headboard of Eddie’s bed smacking into his dresser and the worried look on Eddie’s face. But it’s just like every other aspect of their relationship; it’s silly and playful and they’re probably annoying everyone else around them. 

Maybe it’s the weed they were smoking before or because Richie is already a giggly mess above him but something stirs in Eddie to make him say, “Having this thing feels sort of pointless when I never top.”

“Why, that doesn’t feel good?” Richie replies, gesturing to where Eddie is jerking himself off. 

“It’s not doing anything for you though, is it?”

“I like watching you play with yourself.”

Eddie kind of huffs and looks up at Richie pointedly until it sinks in what he’s egging Richie on for. A wide but hesitant grin grows on Richie’s face.

“Yeah, it’s a fucking shame a dick like that is wasted, huh? A little bitch like you can’t handle using that fucking thing. All you’re good for is getting split open by my cock from both ends.”

And that really, _really_ does something to Eddie and Richie can see it in his face as the feelings in his chest begin to swell, his skin flushing red. Richie grabs his wrist and roughly pulls it away from Eddie’s cock and pins both his hands above his head. He angles his hips downward, pushing Eddie’s knees in towards his chest as he fucks him deeper.

“You don’t need to touch it. All you need is your tight little hole. You might as well have a fucking cunt down there, since your dick is so useless.”

 _Why_ this makes Eddie come so hard is beyond him, but it does. He feels his dick stutter through his first hands-free orgasm as it ripples through him. 

It’s extra sweet when Richie asks if he’s all right after, despite the glowing look of satisfaction Eddie knows is on his face. He simply grins and pulls Richie down to a full kiss, clumsy as all hell as he’s smiling into it.

It’s not all the time that they play like that, but Eddie is so sure he’s found some new sexual awakening. Richie is always just happy to be there and is down for anything, so whatever gets Eddie off equally titillates him in return. 

One thing Eddie can’t help but notice, though, is where Richie’s eyes go when they’re out in public. Eddie doesn’t mind; his own sight drifts over to tall men whose arms are the size of his head. That never bothers Richie, whose body type most resembles _Gumby._ But Eddie could see Richie’s head turn when a cute girl in a skirt would walk by, or when a guy on campus dared to wear shorts higher than his knees. So this gave Eddie another idea that he could only entrust with one other person.

“You want one of my dresses?” 

“Nothing fancy, Beverly, just… something… uh… cute I guess? Or hot? Whatever you think fits me best. Also, could you help me with hair and makeup?”

“What’s the occasion? Night out?”

“Night _in,_ actually…”

Eddie had gotten better over the years about not getting hang ups in regards to his attire. He still won’t wear his short-shorts unless he’s running, but he can confidently walk out in pastel sweaters and overalls and bright polos without caring that the _macho_ dudes on campus will pick on him for it. Stepping into a dress, however, is a whole new territory.

When he looks at himself in the mirror after Bev leaves his dorm, he’s flabbergasted. The silk is hugging his waist and giving him _curves_ and the slickness of it makes his limbs look lithe and elegant, as if he _wasn’t_ the world's biggest klutz to exist (he is). There’s an urge to run outside into the hot sun and feel the heat and breeze between his legs, but he needs to focus on what he’s doing right now. 

All he has to do is wait for Richie. About ten minutes before he knows Richie will be there, he lays on his back and eyes the lube shooter he bought with apprehension. They’ve never used one before, since Richie has usually been so good with foreplay and teasing and taking his time getting Eddie wet and open. For the occasion, Eddie thought it was fitting. So he slides it in as far as it’ll go, squeezes all the lube up there and tosses the medieval looking thing aside where Richie can’t find it. 

Extra lube and a towel were placed on Eddie’s dresser. Bill was explicitly told not to come anywhere near the dorm for several hours. All Eddie _really_ needs is himself, but he’s still anxious about preparation. Just when Eddie is triple-checking that he has everything he needs, Richie’s all too familiar knock is on the door. Eddie lets out a yip, his heart jumping in his chest as he runs to the door to pry it open, stepping aside to let Richie in without showing himself to the hallway.

“Sock on the door already,” Richie teases as he walks into the dorm. “What have I gotten my...self… into…”

Richie trails off as the door is shutting, revealing Eddie standing shyly in his zaffre silk slip dress. His eyes roam all over, trying to take it in; strap hanging off Eddie’s right shoulder, loose fitting over Eddie’s flat chest, snug in the middle, high-riding above Eddie’s knees where his stockings are clinging to a garter hidden where Richie’s eyes can’t see yet. Beverly had been kind enough to outline Eddie’s brown eyes with a crisp black and dark lashes fading into a paler blue eyeshadow that sparkled in the sunlight coming in from the window. 

Trashmouth was at a loss for words.

Apparently, so was Eddie, all his courage and hubris fading in the deafening silence. “Do… you like it?”

“Holy shit,” Richie finally breathed, slowly walking over to Eddie. “You are fucking _gorgeous.”_

Relief spread through him as Eddie giggled shyly up at Richie, who was cupping Eddie’s cheeks before letting his hands roam down Eddie’s arms. “What… what’s the occasion?”

“I love you,” Eddie sighs simply, reaching his arms up around Richie’s neck and standing up on his tippy toes. “That’s all. I just wanna look nice for you. You never get a chance to… get this.”

He doesn’t want Richie to feel bad as he subtly references Richie’s wide spectrum of sexual preferences. He’s never minded that Richie likes women and other men and anything in between or off the grid at all. Sometimes he _does_ feel bad that Richie can’t have Eddie _all_ ways, but Richie has always assured him that Eddie is the _only_ thing he wants.

“God, I love you too. Do _you_ like it?” Richie asks quietly.

“I really do,” Eddie tells him truthfully, happy to see Richie smiling. “And we can even… you know. Roleplay with it.”

“Yeah?”

“Definitely.” Eddie takes a deep breath, thumbing Richie’s chin. “Why don’t you treat me like your pretty little plaything?”

Richie takes a deep breath, slowly walking back with Eddie’s hands in his own. He sits down on the edge of Bill’s bed (they’ll apologize for that _never)_ and looks Eddie straight in the eye. 

“Get on your knees.”

It’s not the first thing Eddie thought about, but his brain is buzzing already with excitement as he drops gracelessly between Richies legs. Eddie fumbles for the zipper and eagerly pulls Richie’s cock out, already rock hard in Eddie’s small hand. Normally, he’d be hungrily slobbering on it, but there’s something so _delicate_ about the way he feels dressed like this. Like, _chaste_ or something, which is ridiculous. Eddie has not had chaste thoughts since the first time he saw a dick in a porn magazine when he was supposed to be staring at the tits on the other page. 

Still, he relishes in the small hiss from Richie above him as he slowly takes just the head of Richie’s dick in his mouth. He sucks almost tenderly on the foreskin before pulling it back with his hand and licking up the slit to taste the precum already beading. He hopes his lipstick looks pretty circling Richie’s dick as he bobs his head up and down. If it was too slow for Richie, Eddie knows he won’t have to ask, because Richie knows by now that Eddie wants Richie to just take what he wants.

“Quit being so fucking shy,” Richie growls, fisting Eddie’s hair and shoving him down to gag on his cock. “Thatta girl,” he chuckles as Eddie starts sputtering drool and tearing up. “Swallow it all down you fucking slut. I know how much your throat is aching for it.”

Eddie’s own dick twitches where it’s bursting through his tight panties; it’s an ache he wants to satiate, but Richie pulls his dick out of Eddie’s mouth and slaps his cheek with his slobbered on cock when Eddie reaches between his legs.

“Leave it alone,” Richie hisses, tightening his grip in Eddie’s hair. He wipes a tear from Eddie’s eye, only to smear Eddie’s makeup down his cheek and let his mascara bleed. “You don’t need to touch yourself. You’re just a hole or me to fuck however I want. You understand?”

Without waiting for Eddie to whimper a feeble _yes,_ Richie laughs as he forces Eddie to nod in the grip of his hand.

“A hole doesn’t need to get off. There’s nothing between your legs worth touching yourself for, ain’t that right?”

“Yes, Daddy,” Eddie whimpers. 

“Unless you have something down there to get Daddy off, it’s pretty fucking pointless, right baby?”

Eddie nods fervently and cries without thinking, “Please fuck my ass—”

Richie smacks him hard across the face and he whines and grinds his hips to rub the friction of his panties against his cock. 

“What was that, sweetheart?”

“Please fuck my cunt,” Eddie corrects. “It’s so wet for you, Daddy.”

“Do you think I fucking care?” Richie whispers harshly, grabbing Eddie’s spit-covered chin roughly in his hand; he uses his thumb to rub across Eddie’s bottom lip, streaking Eddie’s lipstick. Every word is just getting Eddie into a frenzy, especially as lube is leaking out of his ass and dripping down his thighs beneath his dress. “I’m gonna fuck you anyway whether you like it or not. So keep your hands off your useless clit and do what I fucking say.”

Eddie nods fervently, but only for a second before Richie is shoving him back down on his dick, gagging and tearing up. He makes sure to look right up at Richie through his lashes in that way that drives Richie crazy, tears and makeup spilling down his cheek as he lets Richie fuck his throat and hold his head still. When Richie pulls him off again, he’s gasping for breath and begging Richie again because the tingling down his thighs is driving him crazy.

“Think my cock is wet enough for your tight little pussy, baby?” Richie breaths, tapping the side of Eddie’s ruddy cheek with his dick.

“Daddy, I’m already wet,” Eddie cries up at him. “I’m so wet for you, Daddy, it’s gonna stain my dress.”

He doesn’t miss the brief hint of confusion on Richie’s face, but Richie is quick to bend down and scoop him up around his waist, tossing him onto the bed. He lets his legs spread open as Richie dips a hand beneath the hem of his dress and _definitely_ doesn’t miss the way Richie’s breath hitches as he palms up Eddie’s thigh, thumbing the garter as his fingertips graze the lace against Eddie’s ass.

“Are you wearing… _panties?”_

“Uh huh,” Eddie grins, nodding and wishing only he could see Richie’s face. The desperate groan Richie makes is enough, and Richie leans down into his ear for just a moment to break his character and whisper, _“You are so fucking amazing,”_ before biting into Eddie’s earlobe.

Pride swells in Eddie’s chest, followed by a jolt as Richie smacks his ass cheek hard, a strange slapping noise against the slick fabric of the dress. Eddie wants to feel it on his skin, and Richie doesn’t hesitate to hike the dress up Eddie’s hips and start thumbing into the drenched lace. Richie’s noises are guttural animalistic and he teeths the panties off like one, sticking his fingers into the ripped up holes so he can shred whatever fabric is left away.

All that’s left there is Eddie’s open ass, surely glistening for Richie to see. He immediately rubs his thumbs into the hole, making Eddie whimper and buck his hips back. Eddie doesn’t expect to feel Richie’s tongue between his cheeks, hungrily lapping around and flicking the opening of Eddie’s ass. Eddie wiggles his hips, silently begging Richie’s tongue to get deeper, but Richie slaps, not his ass cheek, but right over his hole and catching the back of Eddie’s balls and dick. 

It makes Eddie yelp, jumping away, but Richie grabs his hair and shoves his head back down into the mattress.

“Where the fuck are you going? What — that hurt?” He slaps Eddie like that again, definitely hitting Eddie’s balls on purpose with a sick little giggle. “Shouldn’t that feel good? Isn’t that just your little clit? I thought you were aching to touch it before?”

That floaty feeling Eddie gets sometimes is filling his head and making it difficult to form a comprehensible sentence, so he just sobs. Richie leans down into Eddie’s ear and whispers harshly, “Everything besides your cunt is useless down there anyway, right baby?” He makes Eddie nod with his hand. “So you won’t mind if I give it a little spanking?” 

Richie roughly cups Eddie’s junk and squeezes it tight. Eddie whimpers but doesn’t stop himself from pushing his hips back again, because he’s a fucking brat that is just asking for it.

“God, you’re such a fucking slut.” Richie releases his vice grip and gives Eddie’s dick and balls another hard slap before he shoves two fingers into his dripping ass and Eddie cries out, digging his fingers into the blanket under him. “That’s what you want, huh? Your filthy fucking pussy filled up? Is that why you got all prettied up, to be treated like a fucking whore?”

He doesn’t need to make Eddie nod this time, he just does it willingly as he cries at the sensation of Richie’s fingers fucking him, stretching him out. He’s already so drenched that Richie’s lining his dick up in no time at all, pressing Eddie down with a hand flat on his back, another still gripped tightly in his hair. 

“Your little pussy takes my cock so well, babydoll. You’re such a good girl for Daddy.”

All thoughts of the rest of the dorm are cleared from either of their heads. Eddie is moaning whorishly and sobbing in pleasure as Richie fucks him roughly, pounding the bed into the wall without a care. Richie grabs the back of Eddie’s dress tightly for more leverage and pulls Eddie’s head back to look up straight ahead.

He catches Richie’s eyes in the reflection of a picture frame, the image itself snuffed out as Eddie’s eyes zone in on his own and Richie’s looking back at him. His face is a mess, caked and smeared with glitter and color, cheeks ruddy red and still shining with his own drool and precum.

“You look so fucking pretty getting drunk on my cock, baby,” Richie grunts, squeezing Eddie’s throat in a way Eddie can only describe as affectionately. “You wanna touch yourself, huh?”

Eddie shakes his head in Richie’s grip and Richie laughs in his ear.

“That’s right; just rub that little clit into the bed,” he says, quickening the pace of his fucking Eddie into the mattress. “All you need is my cock in your cunt, ain’t that right baby? Whatever else you have down there is worthless when you can’t get me off from it.”

“Yes, Daddy,” Eddie manages to cry, floating off so high that his eyes roll to the back of his head. He’s so close, _so close,_ he just needs —

“That’s right, you can come. You can come on my cock. Let me see you come.”

Like a tidal wave crashing, Richie’s permission gives way for Eddie to finally feel that sweet release, his body shuddering violently beneath Richie’s weight. What’s left of the front of his panties is so tight on his cock and it’s pressed so firmly into the mattress he can’t even really _feel_ his cum, just relishes in the feeling of Richie’s cock in his ass and the pleasure pulsating through the rest of him.

He can’t process Richie coming until he feels Richie’s hands grabbing his thighs from behind.

“Jesus Christ. I wish I could capture this mental image forever.”

Eddie can just picture it; Richie’s cum trickling out of his hole with all the lube and spit, bits of torn lace hanging onto Eddie’s thighs by the garter still holding up his stockings, blue dress curtaining the curves of Eddie’s hips. He feels Richie leave kisses up and down his skin where it’s still dry, pressing his lips against the nylon hugging Eddie’s legs.

He knows exactly where to get the towel Eddie left and does a quick wipe before rolling Eddie over and peppering kisses along his messy, sticky face.

“You’re so fucking amazing, baby,” he whispers gently, carefully starting to clean off Eddie’s cheeks.

“You messed up all of Bev’s hard work,” Eddie chuckles.

“I’ll accept her fury,” Richie teases, kissing the tip of Eddie’s nose. “God, you look so good. You’re so fucking beautiful.”

“You want me to start dressing like this now?” Eddie smiles.

“You’re always beautiful, Eds,” Richie clarifies. “And you’re so fucking good to me, doll. I seriously can’t get over what a perfect man you are; beautiful, handsome, wonderful, just fucking _perfect.”_

Eddie’s all giggles and getting flustered, shyly turning away as Richie keeps trying to kiss his cheeks and wrap him up in his long limbs. He only fights back playfully for a moment before happily snuggling up into Richie’s chest. Between his legs, Richie helps shimmy off whatever is left of his panties to free his throbbing dick, finally letting it breath.

Richie is _very_ kind to rub him down with lotion all over, once everything is clean and dry again.

“It is still a _very_ pretty cock, you know,” he says, kissing Eddie’s neck. “I don’t want you to hide it _all_ the time. I miss playing with it.”

“It’s all yours to play with, Daddy,” Eddie teases back.

“Good,” Richie grins, pinning Eddie down to kiss him fully on the mouth. “Because next time I’m gonna suck that pretty thing down with my head in your skirt, sweetheart.”

Eddie grins at the mental image of his leg hiked up over Richie’s shoulder and his face buried beneath a petticoat. “You’ve got yourself a fucking date.”


End file.
